Compunds useful as pesticides

ABSTRACT

Compounds useful to control pests are provided.

PRIORITY

This application claims priority from U.S. provisional application60/435,929 which was filed on Dec. 20, 2002.

FIELD OF THE INVENTION

This invention provides compounds that are useful as pesticides.

BACKGROUND OF THE INVENTION

There is an acute need for new pesticides. For example, insects andmites are developing resistance to the insecticides and acaricides incurrent use. At least 400 species of arthropods are resistant to one ormore insecticides. The development of resistance to some of the olderinsecticides, such as DDT, the carbamates, and the organophosphates, iswell known. But resistance has even developed to some of the newerpyrethroid insecticides and acaricides. Therefore, a need exists for newinsecticides and acaricides, and particularly for compounds that havenew or atypical modes of action.

DETAILED DESCRIPTION OF THE INVENTION

In Figure One Q, R¹, R², and R³ have the following meanings.

Q can be any five or six membered carbocyclic or heterocyclic ring, suchas, phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl,pyrazolyl, imidazolyl, thienyl, furanyl, thiazolyl, isothiazolyl,oxazolyl, and isoxazolyl, and including reduced forms of theheterocyclic rings such as tetrahydrofuranyl.

R¹, R², and R³ each independently can be:

-   -   (a) a C₁₋₁₀, branched or unbranched, alkyl, alkoxy, alkenyl,        alkynyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl,        alkylcarbonothioyl, alkoxycarbonyl, alkylthiocarbonyl,        alkoxycarbonothioyl, alkylthiocarbonothioyl, or HC(═NH)—;    -   (b) a C₃₋₁₀, cycloalkyl, or cycloalkenyl;    -   (c) an aryl, heterocyclyl, aryloxy, heterocyclyloxy, arylthio,        heterocyclylthio, arylamino, or heterocyclylamino; or    -   (d) a hydro, hydroxy, mercapto, amino, cyano, formyl, nitro,        halo, or aminocarbonyl.

Additionally, R¹ and R² can be joined together to form a ring, eitherdirectly with a bond between them, or indirectly through one or twolinkage atoms, where such linkage atoms are either carbon, nitrogen,oxygen, or sulfur.

Each member of Q, each member of R¹, R², and R³, and any of the linkageatoms, which may have a hydrogen atom in a certain position, may insteadof having such hydrogen atom, have a:

-   -   (a) a C-₁₋₁₀, branched or unbranched, alkyl, alkoxy, alkenyl,        alkynyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl,        alkylcarbonothioyl, alkoxycarbonyl, alkylthiocarbonyl,        alkoxycarbonothioyl, alkylthiocarbonothioyl, HC(═NH)—,        dialkylphosphonyl, or dialkylphosphatyl;    -   (b) a C₃₋₁₀, cycloalkyl, or cycloalkenyl;    -   (c) an aryl, heterocyclyl, aryloxy, heterocyclyloxy, arylthio,        heterocyclylthio, arylamino, or heterocyclylamino; or    -   (d) a hydro, hydroxy, mercapto, amino, cyano, formyl, nitro,        halo, or aminocarbonyl;        in such position, provided that these substituents are        sterically compatible and the rules of chemical bonding and        strain energy are satisfied. Figure One is a generic structure.        It should be noted that this generic structure can represent,        depending on the substituents used, two generic isomers due to        the presence of the double bond. These two generic isomers can        exist in a dynamic equilibrium with each other and so        interconvert through tautomeric or canonical forms by free        rotation around the relevant bond. This invention comprises all        such interconverting isomers and purified derivatives thereof.        The nature of tautomeric and canonical forms is understood to be        as described in “Advanced Organic Chemistry: Reactions,        Mechanisms and Structure”, 4^(th) edition, J. March ed., John        Wiley and Sons, New York, 1992.

The term “aryl” means a monovalent radical derived by loss of hydrogenfrom an aromatic hydrocarbon. The term heteroaryl means a monovalentradical derived by loss of a hydrogen from a ring structure, where suchring structure contains one or more nitrogen, oxygen, or sulfur atoms.Examples of aryls and heteroaryls include, but are not limited to,phenyl, naphthyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl,pyrrolyl, pyrazolyl, imidazolyl, thienyl, furanyl, thiazolyl,isothiazolyl, oxazolyl, and isoxazolyl, and included are reduced formsof the heteroaryls such as tetrahydrofuranyl.

All salts and esters of these compounds are contemplated as part of thisinvention.

The compounds of the invention are useful for the control of pests suchas, insects and mites. Therefore, the present invention also is directedto a method for inhibiting an insect or mite which comprises applying toa locus of the insect or mite an insect- or mite-inhibiting amount of acompound of this invention. In particular, these compounds controlinsects in the order Homoptera, including the families Aphididae(aphids), Aleyrodidae (whiteflies), Delphacidae (planthoppers), andCicadellidae (leafhoppers). They also control insects in the orderColeoptera (beetles), including the family Chrysomelidae (leaf beetles).Also, they control lepidopterans such as tobacco budworm and cabbagelooper. In particular, other representative pests which may becontrolled by the method of this invention include members of theArthropoda, including mites of the suborders Mesostigmata,Sarcoptiformes, Trombidiformes and Onchychopalpida; sucking and bitinglice of the orders Anoplura and Mallophaga: ticks of the familiesIxodidae and Argasidae: fleas of the families Pulicidae,Ceratophyllidae, and others; Cimex and other Hemiptera; Triatoma andother Heteroptera: and myiasis-related fly larvae and blood suckingadults (including mosquitoes) of the suborders Brachycera, Cyclorrhaphaand Nematocera. Representative also are helminths included in theNematoda (Strongylida, including but not limited to Strongyloidea,Ancylostomatoidea, Trichostrongyloidea and Metastrongyloidea; Ascarida,Ascarisl; Filarlina, such as but not limited to Onchocerca andDirofilaria; Rhabditida; and Trichinellida); Cestoidea, especiallyCyclophyllidea, and Trematoda, including Strigeatoidea such asSchistosoma; Echinostomida such as Fasciola: and Plagiorchiida such asParaqonimus. Other pests which may be controlled by compounds of thisinvention Acanthocephala such as Macracanthorhynchus, Onicola orMoniliformis, and Pentastomida, especially Linguatula; and Protozoa,especially Coccidia such as Elmeria and Plasmodium, Piroplasmea such asBabesia; Toxoplasmea such as Trypanosoma, Trichomonadidae such asTrichomonas and Entamoebidae such as Entamoeba. Illustrative of specificpests of various animals which may be controlled by the method of thisinvention include arthropods such as mites (mesostigmatids, itch. mange,scabies. chiggers), ticks (soft-bodied and hard-bodied), lice (sucking,biting), fleas (dog flea, cat flea, oriental rat flea), true bugs (bedbugs, kissing bugs), bloodsucking adult flies (horn fly, horse fly,stable fly. black fly, deer fly, louse fly, tsetse fly, punkies,mosquitoes), and parasitic fly maggots (bot fly, blow fly, screwworm,cattle grub, fleeceworm); helminths such as nematodes (threadworm,lungworm, hookworm, whipworm, nodular worm, stomach worm, round worm,pinworm, heartworm), cestodes (tapeworms) and trematodes (liver fluke,blood fluke); protozoa such as coccidia, trypanosomes, trichomonads,amoebas and plasmodia; acanthocephalans such as thorny-headed worms; andpentastomids such as tongueworms.

The compounds are useful for reducing populations of insects and mitesand are useful in a method of inhibiting an insect or mite populationwhich comprises applying to a locus of the insect or mite an effectiveinsect- or mite-inactivating amount of a compound of this invention.

The “locus” of insects or mites is a term used herein to refer to theenvironment in which the insects or mites live or where their eggs arepresent, including the air surrounding them, the food they eat, orobjects or materials which they contact. For example, plant-ingestinginsects or mites can be controlled by applying the active compound toplant parts that the insects or mites eat, particularly the foliage.Soil-inhabiting insects such as termites can be controlled by applyingthe active compound to the soil that the insects move through. Insectssuch as fleas that infest animals can be controlled by applying theactive compound to the animal that is infested. Oral administration ofthe compounds of this invention may be performed by mixing the compoundin the animal's feed or drinking water, vitamin or mineral supplement,or by administering oral dosage forms such as drenches, tablets, bolus,salt block or capsules.

It is contemplated that the compounds might also be useful to protecttextiles, paper, stored grain, or seeds by applying an active compoundto such substance.

The term “inhibiting an insect or mite” refers to a decrease in thenumbers of living insects or mites, or a decrease in the number ofviable insect or mite eggs. The extent of reduction accomplished by acompound depends, of course, upon the application rate of the compound,the particular compound used, and the target insect or mite species. Atleast an inactivating amount should be used.

The terms “insect-inactivating amount” and “mite-inactivating amount”are used to describe the amount, which is sufficient to cause ameasurable reduction in the treated insect or mite, population.Generally an amount in the range from about 1 to about 1000 ppm byweight active compound is used. In another embodiment, the presentinvention is directed to a method for inhibiting a mite or insect whichcomprises applying to a plant an effective mite- or insect-inactivatingamount of a compound of this invention.

The compounds of this invention are applied in the form of compositionswhich comprise a compound of this invention and aphytologically-acceptable inert carrier. The compositions are eitherconcentrated formulations which are dispersed in water for application,or are dust or granular formulations which are applied without furthertreatment. The compositions are prepared according to procedures andformulae which are conventional in the agricultural chemical art, butwhich are novel and important because of the presence therein of thecompounds of this invention.

The dispersions in which the compounds are applied are most oftenaqueous suspensions or emulsions prepared from concentrated formulationsof the compounds. Such water-soluble, water-suspendable or emulsifiableformulations are either solids, usually known as wettable powders, orliquids usually known as emulsifiable concentrates or aqueoussuspensions. Wettable powders, which may be compacted to form waterdispersible granules, comprise an intimate mixture of the activecompound, an Inert carrier, and surfactants. The concentration of theactive compound is usually from about 10% to about 90% by weight. Theinert carrier is usually chosen from among the attapulgite clays, themontmorillonite clays, the diatomaceous earths, or the purifiedsilicates.

Effective surfactants, comprising from about 0.5% to about 10% of thewettable powder, are found among the sulfonated lignins, the condensednaphthalenesulfonates, the naphthalenesulfonates, thealkylbenzene-sulfonates, the alkyl sulfates, and nonionic surfactantssuch as ethylene oxide adducts of alkyl phenols.

Emulsifiable concentrates of the compounds comprise a convenientconcentration of a compound, such as from about 50 to about 500 gramsper liter of liquid, equivalent to about 10% to about 50%, dissolved inan inert carrier which is either a water miscible solvent or a mixtureof water-immiscible organic solvent and emulsifiers. Useful organicsolvents include aromatics, especially the xylenes, and the petroleumfractions, especially the high-boiling naphthalenic and olefinicportions of petroleum such as heavy aromatic naphtha. Other organicsolvents may also be used, such as the terpenic solvents including rosinderivatives, aliphatic ketones such as cyclohexanone, and complexalcohols such as 2-ethoxyethanol. Suitable emulsifiers for emulsifiableconcentrates are chosen from conventional nonionic surfactants, such asthose discussed above.

Aqueous suspensions comprise suspensions of water-insoluble compounds ofthis invention, dispersed in an aqueous vehicle at a concentration inthe range from about 5% to about 50% by weight. Suspensions are preparedby finely grinding the compound, and vigorously mixing it into a vehiclecomprised of water and surfactants chosen from the same types discussedabove. Inert ingredients, such as inorganic salts and synthetic ornatural gums, may also be added, to increase the density and viscosityof the aqueous vehicle. It is often most effective to grind and mix thecompound at the same time by preparing the aqueous mixture, andhomogenizing it in an implement such as a sand mill, ball mill, orpiston-type homogenizer.

The compounds may also be applied as granular compositions, which areparticularly useful for applications to the soil. Granular compositionsusually contain from about 0.5% to about 10% by weight of the compound,dispersed in an inert carrier which consists entirely or in large partof clay or a similar inexpensive substance. Such compositions areusually prepared by dissolving the compound in a suitable solvent andapplying it to a granular carrier which has been pre-formed to theappropriate particle size, in the range of from about 0.5 to 3 mm. Suchcompositions may also be formulated by making a dough or paste of thecarrier and compound and crushing and drying to obtain the desiredgranular particle size.

Dusts containing the compounds are prepared simply by intimately mixingthe compound in powdered form with a suitable dusty agriculturalcarrier, such as kaolin clay, ground volcanic rock, and the like. Dustscan suitably contain from about 1% to about 10% of the compound.

The active compositions may contain adjuvant surfactants to enhancedeposition, wetting and penetration of the compositions onto the targetcrop and organism. These adjuvant surfactants may optionally be employedas a component of the formulation or as a tank mix. The amount ofadjuvant surfactant will vary from 0.01 percent to 1.0 percent v/v basedon a spray-volume of water, preferably 0.05 to 0.5 percent. Suitableadjuvant surfactants include ethoxylated nonyl phenols, ethoxylatedsynthetic or natural alcohols, salts of the esters of sulphosuccinicacids, ethoxylated organosilicones, ethoxylated fatty amines, crop oilconcentrates containing high molecular weight paraffinic oils and blendsof surfactants with mineral and vegetable oils.

It is equally practical, when desirable for any reason, to apply thecompound in the form of a solution in an appropriate organic solvent,usually a bland petroleum oil, such as the spray oils, which are widelyused in agricultural chemistry.

Insecticides and acaricides are generally applied in the form of adispersion of the active ingredient in a liquid carrier. It isconventional to refer to application rates in terms of the concentrationof active ingredient in the carrier. The most widely used carrier iswater.

The compounds of the invention can also be applied in the form of anaerosol composition. In such compositions the active compound isdissolved or dispersed in an inert carrier, which is apressure-generating propellant mixture. The aerosol composition ispackaged in a container from which the mixture is dispensed through anatomizing valve. Propellant mixtures comprise either low-boilinghalocarbons, which may be mixed with organic solvents, or aqueoussuspensions pressurized with inert gases or gaseous hydrocarbons.

The actual amount of compound to be applied to loci of insects, mites,and aphids is not critical and can readily be determined by thoseskilled in the art in view of the examples above. In general,concentrations of from-10 ppm to 5000 ppm by weight of compound areexpected to provide good control. With many of the compounds,concentrations of from 100 to 1500 ppm will suffice.

The locus to which a compound is applied can be any locus inhabited byan insect or arachnid, for example, vegetable crops, fruit and nuttrees, grape vines, and ornamental plants.

Because of the unique ability of mite eggs to resist toxicant action,repeated applications may be desirable to control newly emerged larvae,as is true of other known acaricides.

In addition to being effective against mites, aphids, and insects whenapplied to foliage, compounds of this invention have systemic activity.Accordingly, another aspect of the invention is a method of protecting aplant from insects which comprises treating plant seed prior to plantingit, treating soil where plant seed is to be planted, or treating soil atthe roots of a plant after it is planted, with an effective amount of acompound of this invention.

The action of the inventive compounds can be broadened by adding other,for example insecticidally, acaricidally, and/or nematocidally active,ingredients. For example, one or more of the following compounds cansuitably be combined with the compounds of the invention:

-   -   (1) organophosphorus compounds such as acephate, azinphosmethyl,        cadusafos, chlorethoxyfos, chlorpyrifos, coumaphos, dematon,        demeton-S-methyl, diazinon, dichlorvos, dimethoate, EPN,        erthoate, ethoprophos, etrimfos, fenamiphos, fenitrothion,        fensulfothion, fenthion, fonofos, formothion, fosthiazate,        heptenophos, malathion, methamidophos, methyl parathion,        mevinphos, monocrotophos, parathion, phorate, phosalone,        phosmet, phosphamidon, phosphocarb, phoxim, profenofos,        propaphos, propetamphos, prothiofos, pyrimiphos-methyl,        pyrimiphos-ethyl, quinalphos, sulprofos; tebupirimphos,        temephos, terbufos, tetrachlorvinphos, thiafenox, thiometon,        triazophos, and trichlorphon;    -   (2) carbamates such as aldicarb, bendiocarb, benfuracarb,        bensultap, BPMC, butoxycarbocim, carbaryl, carbofuran,        carbosulfan, cloethocarb, ethiofencarb, fenobucarb,        furathiocarb, methiocarb, isoprocarb, methomyl, oxamyl,        pirimicarb, promecarb, propoxur, thiodicarb, and thiofurox;    -   (3) pyrethroids such as acrinathrin, allethrin, beta-cyfluthrin,        bifenthrin, bioresmethrin, cyfluthrin; cyhalothrin;        lambda-cyhalothrin; gamma-cyhalothrin, cypermethrin;        alpha-cypermethrin; zeta-cypermethrin; deltamethrin,        esfenvalerate, fenvalerate, fenfluthrin, fenpropathrin,        flucythrinate, flumethrin, fluvalinate, tau-fluvalinate,        halfenprox, permethrin, protrifenbute, resmethrin, silafluofen,        tefluthrin, tetramethrin, tralomethrin, fish safe pyrethroids        for example ethofenprox, natural pyrethrin, tetramethrin,        s-bioallethrin, fenfluthrin and prallethrin;    -   (4) acylureas, other types of insect growth regulators and        insect hormone analogs such as buprofezin, chromfenozide,        chlorfluazuron, diflubenzuron, fenoxycarb, flufenoxuron,        halofenozide, hexaflumuron, hydroprene, leufenuron, methoprene,        methoxyfenozide, novaluron, pyriproxyfen, teflubenzuron and        tebufenozide,        N-[3,5-dichloro-2-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-N′(2,6-difluorobenzoyl)urea;    -   (5) neonicotnioids and other nicotinics such as acetamiprid,        AKD-1022, cartap, TI-435, clothianidin, MTI-446, dinotefuran,        imidacloprid, nicotine, nitenpyram, thiamethoxam, thiacloprid;    -   (6) macrolides such as avermectins, milbemycins, or spinosyns        for example such as abamectin, ivermectin, milbemycin, emamectin        benzoate and spinosad; and    -   (7) other insecticidal, acaricidal, molluscicidal and        nematocidal compounds or actives such as aldrin, amitraz,        azadirachtin, azocyclotin. bifenazate, bromopropylate,        chlordimeform, chlorfenapyr, chlofentezine, chlorobenzilate,        chlordane, cyhexatin, cyromazin, DDT, dicofol, dieldrin, DNOC,        endosulfan, ethoxazole, fenazaquin, fenbutatin oxide,        fenproximate, beta-fenpyroximate, fipronil, flubenzimine,        hexythiazox, IKI-220, indoxacarb, lindane, methiocarb,        metaldehyde, methoxychlor, neem, petroleum and vegetable oils,        pyridaben, pymetrozine, pyrimidifen, rotenone, S-1812, S-9539,        spirodiclofen, sulfur, tebufenpyrad, tetradifon, triazamate, an        insect-active extract from a plant; a preparation containing        insect-active nematodes, a preparation obtainable from Bacillus        subtilis, Bacillus thuringiensis, a nuclear polyhedrosis virus,        or other like organism genetically modified or native, as well        as synergists such as piperonyl butoxide, sesamax, safroxan and        dodecyl imidazole, and phagostimulants such as cucurbitacin,        sugars and Coax.

EXAMPLES

These examples are provided to further illustrate the invention. Theyare not meant to be construed as limiting the invention.

Example One Preparation of Compound One

A solution of 6.0 g (23.4 mmol) of Preparatory Compound I (J. PesticideSci., 18, 31-40, 1983) in 35 mL of dimethylformamide dimethylacetal washeated at 85-90° C. for 3 hours and was then allowed to cool to roomtemperature, which was about 22° C. The volatiles were removed in vacuoand the resulting oil was triturated under ethyl ether and ethyl acetatewith a small amount of methanol to give 2.2 g (30%) of PreparatoryCompound II as a tan solid.

A solution of 130 mg (0.42 mmol) of Preparatory Compound II in 4 mL ofconcentrated ammonium hydroxide was stirred at room temperature, whichwas about 22° C., for 20 hours. The resulting mixture was concentratedto a residue which was chromatographed on silica gel (230-400 mesh)eluting with 95/5 dichloromethane/methanol to give 80 mg (67%) ofCompound One.

Example Two Alternative Preparation of Compound One

A solution of 200 mg (0.641 mmol) of Preparatory Compound II in 3 mL ofmethanol was treated with 0.32 mL (0.64 mmol) of 2.0 N sodium hydroxide.This mixture was then heated at reflux for 2.5 hours, followed bycooling to about 22° C. The resulting portion was then concentrated toan oil, which was then treated with 0.64 mL (0.64 mmol) of 1.0 Nhydrochloric acid. The resulting mixture was then extracted three timeswith dichloromethane, the combined extracts were then dried over sodiumsulfate and were then concentrated to give 190 mg of a residue which waschromatographed on silica gel to give 130 mg (71%) of Compound One, mp100-103° C.

Example Three Preparation of Compounds One and Two

To a solution of 18.9 mg (0.822 mmol) of sodium metal in 3 mL ofabsolute ethanol was added in one portion 200 mg (0.641 mmol) ofPreparatory Compound II. The contents were stirred at room temperature,which was about 22° C., for 3 hours. The solution was cooled in ice andwas treated with 0.13 mL (296 mg, 2.09 mmol)) of methyl iodide in 1.5 mLof ethanol. After stirring overnight at room temperature, which wasabout 22° C., the mixture was concentrated and the residue waspartitioned between dichloromethane and water. Hydrochloric acid (1.0 N,0.64 mL) was added followed by sodium bicarbonate to give a pH of 10-11.The mixture was extracted three times with dichloromethane, the combinedextracts were dried over magnesium sulfate and were concentrated to give160 mg of an oil which was chromatographed on silica gel using 95/5dichloromethane/methanol as eluant to give 130 mg (71%) of Compound Oneand 10 mg (5%) of Compound Two, mp 163-166° C.

Example Four Preparation of Compound Three

A solution of 255 mg (1.00 mmol) of Preparatory Compound III (EP 163855A1) and 238 mg (2.00 mmol) of dimethylformamide dimethylacetal in 3 mLof dry toluene was heated at 100-110° C. for 6 hours and was thenallowed to cool to room temperature, which was about 22° C. The toluenewas removed in vacuo and the resulting solid was triturated under ethylether to afford 272 mg (88%) of Preparatory Compound IV as a yellowsolid, mp 115-123° C.

A solution of 161 mg (0.521 mmol) of Preparatory Compound IV and 0.286mL (0.573 mmol) of 2.0 N sodium hydroxide in 3 mL of methanol wasstirred at room temperature, which was about 22° C., for 7 hours and wasthen cooled in ice. The resulting solution was then treated with 0.572mL (0.572 mmol) of 1.0 N hydrochloric acid. The precipitate wascollected to afford 90 mg (61%) of Compound Three, mp 196-197° C. (dec).

Example Five Testing with Cotton Aphid (Aphis gossypll)

Alcala cotton plants were grown from seed in 7-cm⁻¹ pots undergreenhouse conditions until they reached 35 to 40 cm in height;approximately four weeks old with 5 to 6 true leaves. The plants werethen stripped of all foliage except for the two uppermost true leaves.Two days prior to application, heavily infested leaf sections from acotton aphid colony were cut and placed on each untreated leaf surface.Over the two days, all stages of the aphids abandon the excised hostmaterial and migrate to the succulent growth, predominantly the lowersurface of the leaves. Plants were checked prior to application for eveninfestation levels. Treatments consisted of 4 replicates (plants) eachwith 2 leaves per plant.

Formulation of technical compound was in a solvent solution. For the toprate of each compound, 20 milligrams of technical material was dissolvedin 2 milliliters (ml) of a 9:1 mixture of acetone:ethanol solvent. Oncedissolved, an additional 18-ml of the solvent mix was added to yield a 1mg/ml spray solution. Additional rates were then prepared by serialdilution.

Application was made by an automated tracksprayer (RC-Insecticide #1,Serial MS-9′-002, MANDEL Scientific Company Ltd.) equipped with a singleTX6 SS hollow cone nozzle to simulate an over-the-top application by aboom sprayer. Spray pressure was set at 50 PSI, and the nozzle head wasset approximately 40 cm above the leaf surface (depending on the leafposition it ranged from 35-45 cm). Track velocity and all other settingswere calibrated to deliver approximately 200 L/ha. After application anddrying, the plants were transferred and kept in controlled environmentuntil assessment.

Assessment of compound efficacy is evaluated by counting all livingnon-winged stage aphids infesting each replicate using a dissectingmicroscope.

The compounds tested in this manner were as follows

The results indicate that the LC90 in grams per hectare for CompoundThree was less than 0.78 grams per hectare, whereas, the LC90 forComparative Compound A was 9.1 grams per hectare. This means nearly 11.7times more Comparative Compound A was needed to reach the LC90 levelthan Compound Three.

Example Six Testing with Sweetpotato Whitefly, Bemisia tabaci

Greenhouse-grown cotton plants (ca. five weeks old, grown in 7×7 cm potscontaining ca. 231 cm³ of potting soil mixture) were prepared forwhitefly infestation by removing all foliage except the first or secondpair of fully expanded true leaves. These plants are then moved into thewhitefly colony room of the insectary (temperature maintained at 27°C.), where they are surrounded by cotton or velvetleaf plants infestedwith all life stages of B. tabaci. Initial movement of B. tabaci adultsonto the prepared cotton plants is encouraged by gently shaking thefoliage of the surrounding infested cotton and velvetleaf foliage usinga 1.5-meter long willow branch. The prepared plants are left in placewithin the whitefly colony, where they are exposed to adult female B.tabaci oviposition for ca. 48 hours.

At the end of the oviposition exposure period, adult whiteflies aredislodged from the prepared plants by passing compressed air just abovethe leaves while the leaves are gently disturbed by hand for ca. 15seconds. The prepared plants, which are now infested with eggs of B.tabaci, are removed from the insectary and any remaining adults areremoved from the foliage with a hand-held vacuum fitted with a cage totrap insects. Infested plants are then selected at random and arrangedinto treatment groups of two or three plants each. Leaves of plants toreceive different treatments are separated by a distance of at least 5cm.

Compounds are applied within 24 hours of removing cotton plants fromexposure to oviposition within the B. tabaci colony. Immediately afterapplication, plants are moved to a holding room with a temperature of30° C. and relative humidity of ca. 60%. Compound efficacy was observedby an assessment at 13 days after application. At this evaluation time,whitefly nymphs that have successfully developed to the third and fourthnymphal stadia can be easily seen on the underside of each cotton leafwith the aid of an illuminated magnifying lens (equipped with a circularfluorescent tube).

Track sprayer application is designed to simulate field application ofcompounds. As in field applications, the equipment is first calibratedto deliver the desired spray volume, in liters/ha. Next, volumes ofspray solution containing known amounts of test compound are prepared,so that when applied at the known liters/ha spray volume, the desired g[Al]/ha rate will be delivered.

The compounds tested in this manner were as follows.

The results indicate that the LC90 in grams per hectare for CompoundThree was less than 2.52 grams per hectare, whereas, the L90 forComparative Compound A was 6.66 grams per hectare. This means nearly 2.7times more Comparative Compound A was needed to reach the LC90 levelthan Compound Three.

Example Seven Testing with Cat Flea (Cntenocephalides felis

Media is prepared by mixing 1 part dried bovine blood, 4 parts grounddog food pellets, and 95 parts clean sand. Compounds are dissolved inacetone and further diluted in acetone to yield the required range ofconcentrations. The acetone solutions are applied to measured amounts ofmedia in small dishes. Final concentrations are expressed as microgramsof compound per gram of media. After the acetone has dried, the treatedmedia is dispensed into small glass vials and infested with 5 to 10 catflea (Cntenocephalides fells) eggs. The vials are loosely capped andheld under controlled conditions for five weeks. Activity is assessedbased on the average number of adult cat fleas present in the treatedvials compared to the average number of adult cat fleas in the media

The compounds tested in this manner were as follows.

The results indicate that Compound One showed 100% control of cat fleasat the 0.1 μg/g rate, whereas Compound Three showed 96% control of catfleas at the 0.1 μg/g rate, and 81% at the 0.01 μg/g rate.

1. A compound according to

wherein Q can be any five or six membered carbocyclic or heterocyclicring, R¹, R², and R³ each independently can be (a) a C₁₋₁₀, branched orunbranched, alkyl, alkoxy, alkenyl, alkynyl, alkylthio, alkylsulfinyl,alkylsulfonyl, alkylcarbonyl, alkylcarbonothioyl, alkoxycarbonyl,alkylthiocarbonyl, alkoxycarbonothioyl, alkylthiocarbonothioyl,HC(═NH)—, (b) a C₃₋₁₀, cycloalkyl, or cycloalkenyl, (c) an aryl,heterocyclyl, aryloxy, heterocyclyloxy, arylthio, heterocyclylthio,arylamino, or heterocyclylamino, or (d) a hydro, hydroxy, mercapto,amino, cyano, formyl, nitro, halo, or aminocarbonyl, R¹ and R² can bejoined together to form a ring, either directly with a bond betweenthem, or indirectly through one or two linkage atoms, where such linkageatoms are either carbon, nitrogen, oxygen, or sulfur, and wherein eachmember of Q, each member of R¹′ R², and R³, and any of the linkageatoms, which may have a hydrogen atom in a certain position, may insteadof having such hydrogen atom, have a (a) a C₁₋₁₀, branched orunbranched, alkyl, alkoxy, alkenyl, alkynyl, alkylthio, alkylsulfinyl,alkylsulfonyl, alkylcarbonyl, alkylcarbonothioyl, alkoxycarbonyl,alkylthiocarbonyl, alkoxycarbonothioyl, alkylthiocarbonothioyl,HC(═NH)—, dialkylphosphonyl, or dialkylphosphatyl, (b) a C₃₋₁₀,cycloalkyl, or cycloalkenyl, (c) an aryl, heterocyclyl, aryloxy,heterocyclyloxy, arylthio, heterocyclylthio, arylamino, orheterocyclylamino, or (d) a hydro, hydroxy, mercapto, amino, cyano,formyl, nitro, halo, or aminocarbonyl, in such position.
 2. Acomposition comprising a compound according to claim 1 and at least oneother active compound where such active compound is at leastinsecticidally, acaricidally, or nematocidally active.
 3. A process ofapplying a compound according to claim 1, or a composition according toclaim 2, to a locus in an amount effective to control pests.
 4. Aprocess of applying a compound according to claim 1, or a compositionaccording to claim 2, to a locus in an amount effective to controlinsects or mites.
 5. A process of topically applying a compoundaccording to claim 1, or a composition according to claim 2, to ananimal in an amount effective to control fleas.
 6. A process of orallyadministering a compound according to claim 1, or a compositionaccording to claim 2, to an animal in an amount effective to controlfleas.